Volume XXVII Issue #2 • An Excerpt From:

Third Winchester
(Opequon)

by Scott C. Patchan

Click Here to view a sample map from this article
Note: All Blue & Gray feature articles are annotated.

Grant laid out an ambitious plan for Sheridan, instructing him to place his army south of Early and to follow him to the death. However, at the time, the Lincoln administration was more concerned with avoiding the defeats and embarrassments that had heretofore been the hallmark of Union efforts in the Shenandoah Valley. After a meeting with the President, Stanton took Sheridan aside and impressed upon him the need for utmost caution and vigilance in the Shenandoah Valley and along the Potomac River line. Grant formally placed Sheridan at the wheel of the Army of the Shenandoah on August 7, 1864, at Monocacy Junction, Maryland. On that same day, Brig. Gen. William W. Averell utterly routed Brig. Gen. John C. McCausland’s Chambersburg raiders at Moorefield, West Virginia.

When Sheridan took over no one in the Union high command knew the precise whereabouts of Early’s command. All that was known for sure was that elements of his command had burned Chambersburg on July 30, and more recently that Confederate infantry had crossed into Maryland. It was only a feint to cover McCausland’s retreat, but few knew that at the time. However, Grant knew that if the Army of the Shenandoah threatened the Valley Pike, Jubal Early’s (left) lifeline to Richmond, the Virginian would soon show himself. Grant sent the army to Harper’s Ferry and Early predictably withdrew from his position near the Potomac River below Martinsburg. Sheridan then set about to gain the pike south of Winchester to sever Early’s communications, but the Virginian remained a step ahead and reached the safety of Fisher’s Hill near Strasburg. When McCausland returned to the Valley, Early had 15,000 troops on hand to confront Sheridan’s effective strength of 26,000 men. Although Sheridan’s force soon grew to 40,000, it had not yet fully assembled in the Shenandoah Valley.

While Sheridan (right) felt out Early’s position, reports filtered into the Ohioan’s headquarters telling of Confederate reinforcements moving from the Culpeper area to the Valley. In response, Sheridan fortuitously detached Brig. Gen. Wesley Merritt’s cavalry toward Front Royal to monitor the situation. By mid-August, Confederate Lt. Gen. Richard H. Anderson had arrived at Front Royal with Maj. Gen. Joseph B. Kershaw’s infantry division, Maj. Gen. Fitzhugh Lee’s cavalry division, and two artillery battalions, numbering about 6,000 men in all. Anderson’s arrival raised the Confederate strength to 21,000 soldiers, including 15,000 elite troops from the Army of Northern Virginia who had long since gotten used to fighting against unfavorable odds. Only this time Sheridan barely outnumbered those Confederates, and he wisely fell back and avoided entrapment at Strasburg.

In addition to Sheridan’s scouting reports, Grant rushed an urgent message to Sheridan via Col. Nicholas Chipman of the War Department. Given the problems with communications experienced thus far that summer and the sensitivity of Grant’s message, Chipman physically carried it to the Valley, riding through Snicker’s Gap. Grant wrote, “It is now certain two divisions of infantry have gone to Early and some cavalry and twenty pieces of artillery.” Grant warned that Sheridan “must be cautious and act on the defensive until movements here force them to detach [troops] to [Richmond/Petersburg].” This message coupled with Stanton’s cautions governed Sheridan’s actions for the next month until Early detached troops back to Lee.2 Sheridan promptly withdrew his army toward Harper’s Ferry. As for Colonel Chipman, he remained in the Valley, observing Sheridan’s every move and reporting his opinions to Secretary of War Stanton.

Robert E. Lee had high hopes for Anderson’s force. He originally wanted Anderson to stir up trouble in the Virginia Piedmont east of the Blue Ridge, where he would pose a threat to Washington. Ideally, Lee hoped that Sheridan would split his force and then Early and Anderson could unite and defeat the Federals in detail. In the end, however, Early convinced Anderson to forego the operations east of the Blue Ridge and instead join him in the Valley. Anderson’s force marched through Chester Gap and entered Front Royal on August 15. He sent Fitz Lee’s cavalry across the forks of the Shenandoah River on August 16 to drive off Merritt’s outposts at Guard Hill near Front Royal and reinforced him with Brig. Gen. William T. Wofford’s Georgia infantry brigade. The Southerners pushed north toward Merritt’s encampment near Cedarville only to be routed by Brig. Gen. George A. Custer’s and Col. Thomas C. Devin’s brigades. The Federals captured 300 prisoners and several battle flags, driving Wofford’s Georgians back through the deep waters of Crooked Run and prompting Confederate wags to joke that “Wofford swung his right and made a water haul.”